Dimethylformamide → HCID 11774683, compound

HRID 2373908Notes

Reaction equation

HRID 2373908 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)=[N:9][C:10]=2[C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1.[C:22]([O-:25])([O-])=O.[Cs+].[Cs+].CN([CH:31]=[O:32])C>>[CH3:22][O:25][C:31](=[O:32])[C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:10][O:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:10]3[N:9]=[C:8]([CH:18]4[CH2:21][CH2:20][CH2:19]4)[N:4]4[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=34)[CH:12]=2)[CH:16]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 10796Cesium carbonateHCID 11716093HCID 11716093, compound

Product 1

HCID 11774683HCID 11774683, compound

Procedure

A solution of 3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenol (2.87 g, 10.2 mmol) in DMF was charged with Cs2CO3 (4.98 g, 15.3 mmol) and stirred at rt for 30 min. A DMF solution of methyl (3-bromomethyl)benzoate (2.33 g, 10.2 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at rt under nitrogen. The crude product was placed under high vacuum to remove the residual DMF. The product was then purified using silica gel column chromatography (1% NH3 in MeOH:CH2Cl2). The product was recrystalized with CH2Cl2 and hexanes to yield the title compounds as a white solid; 1H NMR (CDCl3, 400 MHz) δ 2.00-2.07 (m, 1H), 2.11-2.22 (m, 1H), 2.45-2.52 (m, 2H), 2.58-2.68 (m, 2H), 3.76-3.85 (m, 1H), 3.93 (s, 3H), 5.18 (s, 2H), 7.01-7.04 (m, 2H), 7.10-7.11 (m, 1H), 7.24-7.29 (m, 2H), 7.38-7.49 (m, 2H), 7.65 (d, J=7.6 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H), 8.13 (s, 1H); MS (ES+): m/z 429.18 (100) [MH+].

Workup

  1. stirringThe reaction mixture was stirred overnight at rt under nitrogen
  2. customto remove the residual DMF
  3. customThe product was then purified
  4. customThe product was recrystalized with CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-1b2feff9103a41feba5a3b5d1139fa64
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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